What does transitioning to a freelance writing lifestyle look like?

I work as a caretaker/cleaner for an Airbnb from 11 to 3, 7 days a week. But usually, there is only an hour or two of work. each day. I do a little house and pet sitting on the side too. So it is a pretty cushy gig.

I work as a caretaker/cleaner for an Airbnb from 11 to 3, 7 days a week. But usually, there is only an hour or two of work. each day. I do a little house and pet sitting on the side too. So it is a pretty cushy gig.

I had a second housekeeping position that took up ten hours per week, but after a couple of months of doing the freelancing I had replaced that income and was able to quit the second cleaning gig.

It isn’t glamorous but it gives me lots of time to work on my writing and wellness blog as well as working on some art projects. I quit a full-time job at a tech company in Silicon Valley because I wanted to start my own business. Part-time jobs like cleaning and organizing have given me the time I need to work on the business and start making money from it.

How I got here from working full-time jobs that sucked

I first started looking into having an online remote business when I was teaching Pilates in Sebastopol CA. I had gotten myself another one of my amazing free living arrangements with a 98-year-old woman who needed someone around in the evenings. I was burnt out on teaching Pilates and looking for something new that was online so that I had the freedom so I could live anywhere I wanted to when I wanted to.

The Pilates studio politics were frustrating, and I had never really enjoyed teaching. So after 15 years of teaching, I finally quit and took up a seasonal no-pressure vacation rental cleaning job while I tried to market my art online and tried my hand at selling used books on Amazon FBA.

Using time wisely at my no-pressure cleaning gig

I cleaned by myself about 4 hours per day, but sometimes I cleaned with a crew if we had a big house to get done in the 4-hour window. I have always been entrepreneurial and have sold art at fairs, and made a living selling hand-painted T-shirts in the past as well as freelancing as a commercial artist.

I was the only one on the vacation rental crew to listen to podcasts on my smartphone while working. I thought it was odd that people would spend 4 hours cleaning houses 7 days a week all summer, without doing any kind of educational listening. I would listen to Steve Chuo from My Wife Quit Her Job, Side Hustle, the Fizzle podcast, Pat Flynn, and anything and everything about how to start an online business and become a creative entrepreneur.

I tried Amazon FBA but it wasn’t for me

Amazon FBA was really fun. I loved searching through thrift stores for books, toys, and games to send to the Amazon warehouses to sell, but I couldn’t get enough momentum to do more than break even. If I wanted to make money I would have to start buying a lot of new stuff online to drop ship and this didn’t appeal to me.

I wanted to do something more personal and more creative. I was spending 60 hours per week finding, shrinking wrapping and shipping stuff but I was still only breaking even when I ran out of funds.

Trying things until I found something that worked

I wasn’t having much luck selling art on Saatchi Art and other online markets though I had ideas I wanted to develop. I really wanted to find a way to earn more money while being location independent while developing my creative ideas.

I sucked at coding

Next, I decided to learn to code. It seemed logical and I heard you could make a great living at coding and hey, I had just moved back to the heart of Silicon Valley. I took courses on Skillcrush, which is a female-positive platform for learning tech skills. I found that I was not learning fast enough and didn’t have enough math background to get beyond CSS.

Though I really like coding I was never great at it and it didn’t come easily for me. I even got a job at Apple contracted through another company, but it was Apple. But life is short and my heart wasn’t in it so I quit and kept looking for a way to build an online business.

I have always been a decent writer

I was already a decent writer and realized there might be something there that I could build on. At Skillcrush they suggested looking into other roles in the tech world if coding wasn’t your thing. There are so many creative positions that support the tech industry. So I reevaluated my skills.

I saw an ad for the AWAI “barefoot writers” course on my Gmail feed and clicked on it even though I never click on those ads. Something about the AWAI images of people in bikinis sunning on the beach while tapping away on their laptops looked fake, or too good to be true. I kept searching for freelance writing information and found Joran Roper’s site and Ed Gandia, another favorite of mine.

I have since joined a B2B (business to business writers) LinkedIn group to learn about B2B (business to business) writing with one of the teachers from AWAI, Gordon Graham, and will probably take his B2B course soon. AWAI is legit but it has really dated imagery and headlines on the site which threw me off at first.

The first course I took was Jordan Roper’s Cold Emailing Course, which is excellent for beginners and gives you a lot of direction and structure. I began to think about a niche because Roper said it was much easier to market if you specialized.

I settled on holistic health since I have a background in teaching fitness and pilates and was a massage therapist for 20 years. I tried a couple of specialties before I ended up niching down to plant-based nutrition for my main focus with other related topics.

I love Affiliate marketing

I came across the Create and Go affiliate marketing courses by Alex and Lauren, this 20 something couple who are grossing 6 figures every month and decided that instead of freelancing, it would be more fun to write for myself and sell affiliate products on my own site using the Create and Go model of Pinterest marketing to get started.

I was worried about working with companies as a freelancer since I had experienced payment delays and other drama, as a freelance illustrator and designer in the past.

I was enjoying writing and researching and building sites and designing graphics. Even though I was working on my business every spare moment it didn’t feel like work. And I loved learning about marketing.

But I was still not bringing in enough money to quit my job and be location independent and have time to build my art projects, and a vegan eco-village, which is my dream.

It turned out that going directly into building my own platform, marketing affiliate products, and trying to come up with products and courses of my own is a long process. I wanted to start bringing in enough to cut back on my hours at my day job but it wasn’t consistent enough.

Reevaluating my path…again!

I decided to spring for B-School even though I couldn’t really afford more course fees on top of my other expenses, and I had already bought a disgraceful number of courses over the past 6 years. I consider myself a course junky. But it’s better than heroin or crack.

B-school was worth it because it made me see that I needed to offer a service and just get going with making money right away and then go back later and refine things as I went along. Marie Forleo is another awesome woman who is bushwacking a new path for us with tons of free resources on her site.

Jordan Roper and Jon Morrow also mentioned that freelancing was the easiest way to get started while you build your platform and become an expert in your niche. Roper wrote for tech blogs while she grew her niche as a writing expert. And Jon Morrow got his start editing marketing blogs so he learned what they look for as an insider.

I am not giving up on affiliate marketing and making money directly from my own sites and my own creations. I am still carving out time and working on those projects because I love doing it. But for now, my main focus is on becoming a high-earning freelance writer.

My free consult with Ash Aimbridge

Ash Aimbridge generously offered a free 45-minute consult to anyone who signed up for B-School using her affiliate link. She was wonderfully down to earth, funny, and sweet and really helped me to evaluate my freelance writing offerings and niche down.

After my consultation with Ash, I spent a couple of weeks updating my sites, and moved the nutrition site back to SiteGround from Flywheel and audited the articles. I am still working on rewriting and refocusing my health site, so it works better. I began reworking my articles to include more research as a showcase for my expertise as a freelance writer and researcher.

I had spent a few months on the Fizzle.com monthly learning platform going through some of their business courses and had tried Flywheel for my health site because they were offering it as part of their monthly course package.

I found that Flywheel was too advanced and cumbersome for where I am right now. Siteground (my affiliate link) is easy to use and allows me to have multiple sites on one hosting platform. If my audience gets so big that I need to move to dedicated WordPress hosting I will deal with it then.

Don’t be afraid to try different niches

Around the same time as B-School, I found Elna Cain’s blog and course on making your first $1000 as a freelance writer. Cain encourages trying different niches when you are starting out. Cain had a lot of good ideas on how to start getting work. As soon as I implemented her ideas for pitching, I got my first freelance gig and earned my first $1400 in a little over a month.

Many of my freelance gigs have not been in my exact “niche”, but the point is my confidence is up because I am learning on-the-job and getting paid. This is giving me confidence and hope so I can continue to work toward my goals and continue pitching for more freelance writing jobs.

I haven’t quit my day job yet, but I can see the end of the tunnel

I am living in Silicon Valley where rents are high. But I have been incredibly lucky. I have not had to pay rent in over 4 years because I have found alternative various situations. I have been able to stay in the vacant apartments at my BNB job for the past year and a half so I only end up couch-surfing once in a while.

A long line of RVs in Mountain View CA, where contractors live while they work in Silicon Valley

My three-year plan

I am learning to write white papers and do whitepaper layout and design using Gordon Graham’s book and linked in learning so that I can earn more per hour with B2B clients than you can with B2C (business to consumer) blogging.

Means goals and ends goals

Freelance writing for B2B is a means goal. I have other creative projects I want to complete but I know they may never be big earners or it may be a long time before they start bringing in money. I am working on a young adult novel and a line of art and figurines that I want to market just because those are my ends goals or creative passion projects.

But I learned from B-school that you don’t have to make money with everything you do and you don’t have to throw something out just because it isn’t profitable. Find things that are profitable that you enjoy that still give you the flexibility, funding, and time to do your passion projects.

My Skoolie short bus project

I plan to get a “skoolie” short bus and convert it to veggie oil, gut it and add insulation, a floor, bed, a workspace, and a kitchenette, like an RV, only way less expensive and a lot more durable. And so much cooler looking too!

If you have been thinking of going on the road as a location-independent-entrepreneur, Heath and Alyssa have an in-depth blog with lots of resources on how to get started with the RV lifestyle.

It turns out you can buy a used school bus for under $5000 at public auctions because schools get funding to upgrade their buses every few years.

You still have to put in a few thousand to wire it for solar and wifi and build it out. But it still costs a lot less than an RV or a fancy stealth van build. (Everyone knows you are living in a stealth van anyway, because why else would there be a fan going and a roof vent?)

Diesel is best because those engines last a long time and can be converted to biodiesel or run on veggie oil from fast-food restaurants. I plan on adding solar panels, and 2 or three types of redundant Wi-Fi so I can work from national parks and rural areas some of the time.

In Silicon Valley, a lot of people live in vans and RVs while they work in the area as contractors. The rent for a single tiny room can easily run you $1500 per month if you can find anything that small. There are a lot of public lands across the US where you can camp for free.

Government Agency Auctions

I am planning to visit permaculture, and climate change sustainability projects around the US and write articles and post podcasts between my freelancing assignments. Eventually, I hope to find or build a sanctuary ecovillage or find a cohousing community with creative types who want to live inexpensively, and sustainably with gardens and tiny houses. Hey! I’m a hippy, what can I say?

Life balance can be a challenge

All in all, I am pretty happy with the process that is unfolding, and with my progress over the last year or two. I am feeling a little isolated because of working so much on my own but I am enjoying life a lot.

I am a little out of balance because I have been so focused on building the business. I need to start getting out to meetups, networking and start building more of a community. There are all kinds of great groups where I am living right now; toastmasters, entrepreneurs, hiking, dancing, etc.

I go to yoga class a few times a week and I just signed up to volunteer for a literacy program teaching reading skills. I live in a gorgeous area and get to go for long walks every morning in nature on local trails. I am on the waiting list for our community gardens.

I work as a caretaker/cleaner for an Airbnb from 11 to 3, 7 days a week. But usually, there is only an hour or two of work. each day. I do a little house and pet sitting on the side too. So it is a pretty cushy gig.

I had a second housekeeping position that took up ten hours per week, but after a couple of months, of doing the freelancing I had replaced that income and was able to quit the second cleaning gig.

It isn’t glamorous but it gives me lots of time to work on my writing and wellness blog as well as working on some art projects. I quit a full-time job at a tech company in Silicon Valley because I wanted to start my own business. Part-time jobs like cleaning and organizing have given me the time I need to work on the business and start making money from it.

How I got here from working full-time jobs that sucked

I first started looking into having an online remote business when I was teaching Pilates in Sebastopol CA. I had gotten myself another one of my amazing free living arrangement with a 98-year-old woman who needed someone around in the evenings. I was burnt out on teaching Pilates and looking for something new that was online so that I had the freedom so I could live anywhere I wanted to when I wanted to.

The Pilates studio politics were frustrating, and I had never really enjoyed teaching. So after 15 years of teaching, I finally quit and took up a seasonal no-pressure vacation rental cleaning job while I tried to market my art online and tried my hand at selling used books on Amazon FBA.

Using time wisely at
my no-pressure cleaning gig

I cleaned for another Airbnb company a few years ago. I cleaned by myself about 4 hours per day, but sometimes I cleaned with a crew if we had a big house to get done in the 4-hour window. I have always been entrepreneurial and have sold art at fairs, and made a living selling hand-painted T-shirts in the past as well as freelancing as a commercial artist.

I was the only one on the vacation rental crew to listen to podcasts on my smartphone while working. I thought it was odd that people would spend 4 hours cleaning houses 7 days a week all summer, without doing any kind of educational listening. I would listen to Steve Chuo from My Wife Quit Her Job,Side Hustle, the Fizzle podcast, Pat Flynn, and anything and everything about how to start an online business and become a creative entrepreneur.

I tried Amazon FBAbut it wasn’t for me

Amazon FBA was really fun. I loved searching through thrift stores for books, toys, and games to send to the Amazon warehouses to sell, but I couldn’t get enough momentum to do more than break even. If I wanted to make money I would have to start buying a lot of new stuff online to drop ship and this didn’t appeal to me.

I wanted to do something more personal and more creative. I was spending 60 hours per week finding, shrink wrapping and shipping stuff but I was still only breaking even when I ran out of funds.

Trying things until I found something that worked

I wasn’t having much luck selling art on Saatchi Art and other online markets though I had ideas I wanted to develop. I really wanted to find a way to earn more money while being location independent while developing my creative ideas.

I sucked at coding

Next, I decided to learn to code. It seemed logical and I heard you could make a great living at coding and hey, I had just moved back to the heart of Silicon Valley. I took courses on Skillcrush, which is a female-positive platform for learning tech skills. I found that I was not learning fast enough and didn’t have enough math background to get beyond CSS.

Though I really like coding I was never great at it and it didn’t come easily for me. I even got a job at Apple contracted through another company, but it was Apple. But life is short and my heart wasn’t in it so I quit and kept looking for a way to build an online business.

I have always been a
decent writer

I was already a decent writer and realized there might be something there that I could build on. At Skillcrush they suggested looking into other roles in the tech world if coding wasn’t your thing. There are so many creative positions that support the tech industry. So I reevaluated my skills.

I saw an ad for the AWAI “barefoot writers” course on my Gmail feed and clicked on it even though I never click on those ads. Something about the AWAI images of people in bikinis sunning on the beach while tapping away on their laptops looked fake, or too good to be true. I kept searching for freelance writing information and found Joran Roper’s site and Ed Gandia, another favorite of mine.

I have since joined a B2B (business to business writers) LinkedIn group to learn about B2B (business to business) writing with one of the teachers from AWAI, Gordon Graham, and will probably take his B2B course soon. AWAI is legit but it has really dated imagery and headlines on the site which threw me off at first.

Update: 2020: I took Gordon’s White Paper course through AWAI and it was legit. I learned a lot of useful things to get going as a white paper writer.

The first course I took was Jordan Roper’s Cold Emailing Course, which is excellent for beginners and gives you a lot of direction and structure. I began to think about a niche because Roper said it was much easier to market if you specialized.

I settled on holistic health since I have a background in teaching fitness and pilates and was a massage therapist for 20 years. I tried a couple of specialties before I ended up niching down to plant-based nutrition for my main focus with other related topics.

I loveAffiliate marketing

I came across the Create and Go affiliate marketing courses by Alex and Lauren, this 20 something couple who are grossing 6 figures every month and decided that instead of freelancing, it would be more fun to write for myself and sell affiliate products on my own site using the Create and Go model of Pinterest marketing to get started.

I was worried about working with companies as a freelancer since I had experienced payment delays and other drama, as a freelance illustrator and designer in the past.

I was enjoying writing and researching and building sites and designing graphics. Even though I was working on my business every spare moment it didn’t feel like work. And I loved learning about marketing.

But I was still not bringing in enough money to quit my job and be location independent and have time to build my art projects, and a vegan eco-village, which is my dream.

It turned out that going directly into building my own platform, marketing affiliate products, and trying to come up with products and courses of my own is a long process. I wanted to start bringing in enough to cut back on my hours at my day job but it wasn’t consistent enough.

Reevaluating my path…again!

I decided to spring for B-School even though I couldn’t really afford more course fees on top of my other expenses, and I had already bought a disgraceful number of courses over the past 6 years. I consider myself a course junky. But it’s better than heroin or crack.

B-school was worth it because it made me see that I needed to offer a service and just get going with making money right away and then go back later and refine things as I went along. Marie Forleo is another awesome woman who is bushwacking a new path for us with tons of free resources on her site.

Jordan Roper and Jon Morrow also mentioned that freelancing was the easiest way to get started while you build your platform and become an expert in your niche. Roper wrote for tech blogs while she grew her niche as a writing expert. And Jon Morrow got his start editing marketing blog so he learned what they look for as an insider.

I am not giving up on affiliate marketing and making money directly from my own sites and my own creations. I am still carving out time and working on those projects because I love doing it. But for now, my main focus is on becoming a high-earning freelance writer.

My free consult with
Ash Aimbridge

Ash Aimbridge generously offered a free 45-minute consult to anyone who signed up for B-School using her affiliate link. She was wonderfully down to earth, funny, and sweet and really helped me to evaluate my freelance writing offerings and niche down.

After my consult with Ash, I spent a couple of weeks updating my sites, and moved the nutrition site back to SiteGround from Flywheel and audited the articles. I am still working on rewriting and refocusing my health site, so it works better. I began reworking my articles to include more research as a showcase for my expertise as a freelance writer and researcher.

I had spent a few months on the Fizzle.com monthly learning platform going through some of their business courses and had tried Flywheel for my health site because they were offering it as part of their monthly course package.

I found that Flywheel was too advanced and cumbersome for where I am right now. Siteground (my affiliate link) is easy to use and allows me to have multiple sites on one hosting platform. If my audience gets so big that I need to move to dedicated WordPress hosting I will deal with it then.

Don’t be afraid to try different niches

Around the same time as B-School, I found Elna Cain’s blog and course on making your first $1000 as a freelance writer. Cain encourages trying different niches when you are starting out. Cain had a lot of good ideas on how to start getting work. As soon as I implemented her ideas for pitching, I got my first freelance gig and earned my first $1400 in a little over a month.

Many of my freelance gigs have not been in my exact “niche”, but the point is my confidence is up because I am learning on-the-job and getting paid. This is giving me confidence and hope so I can continue to work toward my goals and continue pitching for more freelance writing jobs.

I haven’t quit my day
job yet, but I can see the end of the tunnel

I am living in Silicon Valley where rents are high. But I have been incredibly lucky. I have not had to pay rent in over 4 years because I have found alternative situations. I have been able to stay in the vacant apartments at my BNB job for the past year and a half so I only end up couch-surfing once in a while.

A long line of RVs in Mountain View CA, where contractors live while they work in Silicon Valley

My three-year plan

I am learning to write white papers and do whitepaper layout and design using Gordon Graham’s book and linked in learning so that I can earn more per hour with B2B clients than you can with B2C (business to consumer) blogging.

Means goals and ends
goals

Freelance writing for B2B is a means goal. I have other creative projects I want to complete but I know they may never be big earners or it may be a long time before they start bringing in money. I am working on a young adult novel and a line of art and figurines that I want to market just because those are my ends goals or creative passion projects.

But I learned from
B-school that you don’t have to make money with everything you do and you don’t
have to throw something out just because it isn’t profitable. Find things that
are profitable that you enjoy that still give you the flexibility, funding, and
time to do your passion projects.

My Skoolie short bus project

I plan to get a “skoolie” short bus and convert it to veggie oil, and dsolar power. I will have to gut it and add insulation, a floor, bed, a workspace, and a kitchenette, like an RV, only way less expensive and a lot more durable. And so much cooler looking too!

If you have been thinking of going on the road as a location-independent-entrepreneur, Heath and Alyssa have an in-depth blog with lots of resources on how to get started with the RV lifestyle.

It turns out you can buy a used school bus for under $5000 at public auctions because schools get funding to upgrade their buses every few years.

You still have to put in a few thousand to wire it for solar and wifi and build it out. But it still costs a lot less than an RV or a fancy stealth van build. (Everyone knows you are living in a stealth van anyway, because why else would there be a fan going and a roof vent?)

Diesel is best because those engines last a long time and can be converted to biodiesel or run on waste veggie oil from fast-food restaurants. I plan on adding solar panels, and 2 or three types of redundant Wi-Fi so I can work from national parks and rural areas some of the time.

In Silicon Valley, a lot of people live in vans and RVs while they work in the area as contractors. The rent for a single tiny room can easily run you $1500 per month if you can find anything that small. There are a lot of public lands across the US where you can camp for free.

Government Agency Auctions

I am planning to visit permaculture, and climate change projects around the US and write articles and post podcasts between my freelancing assignments. Eventually, I hope to find or build a sanctuary ecovillage or find a cohousing community with creative types who want to live inexpensively, and sustainably with gardens and tiny houses. Hey! I’m a hippy, what can I say?

Life balance can be a challenge

All in all, I am pretty happy with the process that is unfolding, and with my progress over the last year or two. I am feeling a little isolated because of working so much on my own but I am enjoying life a lot.

I am a little out of balance because I have been so focused on building the business. I need to start getting out to meetups, networking and start building more of a community. There are all kinds of great groups where I am living right now; toastmasters, entrepreneurs, hiking, dancing, etc.

I go to yoga class a few times a week and I just signed up to volunteer for a literacy program teaching reading skills. I live in a gorgeous area and get to go for long walks every morning in nature on local trails. I am on the waiting list for our community gardens.

Support Me on Patreon

Disclosure: This site contains affiliate links, meaning we receive a commission if you decide to make a purchase through my links, at no additional cost to you. Please read my disclosure for more info.